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Hydrochlorination of acetylene using a supported gold catalyst: A study of the reaction mechanism

Conte, Marco, Carley, Albert Frederick, Heirene, Clare, Willock, David James, Johnston, Peter, Herzing, Andrew A., Kiely, Christopher J. and Hutchings, Graham John 2007. Hydrochlorination of acetylene using a supported gold catalyst: A study of the reaction mechanism. Journal of Catalysis 250 (2) , pp. 231-239. 10.1016/j.jcat.2007.06.018

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A detailed study of the hydrochlorination of acetylene and higher alkynes using a supported gold catalyst is described and discussed. A series of reactions using sequential exposure of the catalysts to C2H2 and HCl demonstrate that exposure to HCl before reaction of C2H2/HCl leads to enhanced activity, whereas exposure to C2H2 leads to deactivation. The reaction of higher alkynes is affected by steric factors, with the following trend in activity: acetylene (ca. 40% conversion) ≫ hex-1-yne (10%) > phenyl acetylene (7%) > hex-2-yne (2%). Using 1H NMR spectroscopy, we found that for hex-1-yne and phenyl acetylene, the anti-Markovnikov product is formed by anti-addition of HCl, but the Markovnikov products are equivalent for syn- and anti-addition of HCl. Thus, we investigated the reaction using deuterated substrates and confirmed that the products are formed by the anti-addition of HCl. The reaction mechanism is discussed in detail.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Cardiff Catalysis Institute (CCI)
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: Gold catalysis; Catalyst reactivation; Acetylene hydrochlorination
Publisher: Elsevier
ISSN: 0021-9517
Last Modified: 26 Oct 2021 01:21

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